Hydrochloric Acid → 4-(1-Hydroxymethyl-heptyl)-benzoic acid

HRID 658308Notes

Reaction equation

HRID 658308 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:17][OH:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCCC1.C(OCC)C.O>[OH:18][CH2:17][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:19])=[O:2])=[CH:9][CH:8]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 674861584-(1-Hydroxymethyl-heptyl)-benzoic acid methyl ester

Product 1

HCID 674860954-(1-Hydroxymethyl-heptyl)-benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Hydroxymethyl-heptyl)-benzoic acid methyl ester (3.46 g, 12.1 mmol) is dissolved in tetrahydrofuran (40 mL) and 5N sodium hydroxide (10 mL) is added. The reaction may be monitored by HPLC and is complete within 8 h. The reaction is neutralized with 5N HCl (10 mL), and diluted with diethyl ether and water. The two phases are separated, and the organic layer is washed, dried, and concentrated to provide the title compound which is used without further purification. MS (ES): 249.3 [M+H]−.

Workup

  1. customThe reaction
  2. customThe two phases are separated
  3. washthe organic layer is washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e655fa8e8ec404e979ceb12c27e55c9
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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