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Trimethyl orthoformate → 2-(2-Bromophenyl)acetaldehyde dimethylacetal

HRID 652006
Notes
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Reaction equation

HRID 652006 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]C=O.[CH:11](OC)([O:14][CH3:15])[O:12][CH3:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].[Cl-].[Na+].O>CO.C(OCC)C>[CH3:13][O:12][CH:11]([O:14][CH3:15])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 114241802-(2-Bromophenyl)acetaldehydeHCID 131715167NaOH brine

Product 1

HCID 110321302-(2-Bromophenyl)acetaldehyde dimethylacetal

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10.0 grams (0.05 mole) of 2-(2-bromophenyl)acetaldehyde (from the above preparation and another similar preparation) in 50 milliliters of dry methanol, was added 50 milliliters of trimethyl orthoformate and 0.25 gram of p-toluenesulfonic acid monohydrate and the resulting mixture was heated at reflux temperature for 3.5 hours. At the end of this period, the reaction mixture was cooled and 100 milliliters of diethyl ether and 50 milliliters of a 1:1 solution of 50 percent aqueous sodium hydroxide/brine were added. The ether solution was mechanically separated, washed, dried and stripped on the rotary evaporator to obtain 2-(2-bromophenyl)acetaldehyde dimethylacetal intermediate as a yellow oil. The latter was distilled to obtain 10.5 grams (85 percent yield) of purified product as a clear oil, b.p. 65°-67° /0.2 mm.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux temperature for 3.5 hours
  3. temperatureAt the end of this period, the reaction mixture was cooled
  4. customThe ether solution was mechanically separated
  5. washwashed
  6. customdried
  7. customstripped on the rotary evaporator

Sources & evidence

ORD record
ord-d30b109b23a7433daa00e212c9d04755
Source dataset
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04670443

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes