Benzene → HCID 21474561, compound

HRID 1756433Notes

Reaction equation

HRID 1756433 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([OH:14])[CH:5]=[CH:4][C:3]1=2.[Cl:16][C:17](OC(Cl)(Cl)Cl)=[O:18].C1C=CC=CC=1.C(N(CC)CC)C>O>[Cl:16][C:17]([O:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)=[O:18]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 10426DiphosgeneHCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 21474561HCID 21474561, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.1 g (20 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol, 1.2 ml of trichloromethyl chloroformate and 40 ml of benzene are introduced into a round-bottomed flask. 3 ml (21 mmol) of triethylamine are added dropwise and the mixture is stirred at room temperature for twelve hours. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and hexane (40:60). After evaporation of the solvents, 4 g (75%) of the expected chloroformate are collected in the form of a colorless oil.

Workup

  1. extractionthe mixture is extracted with ethyl ether
  2. customthe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column
  7. washeluted with a mixture of dichloromethane and hexane (40:60)
  8. customAfter evaporation of the solvents, 4 g (75%) of the expected chloroformate
  9. customare collected in the form of a colorless oil

Sources & evidence

ORD record
ord-fbc6657477b343d8987f4d653aafa89a
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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