Sulfuric Acid → 2-Chloro-N-[(6-hydroxy-2,3-dihydro-1H-inden-5-yl)methyl]acetamide

HRID 364908

Reaction equation

HRID 364908 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[Cl:11][CH2:12][C:13]([NH:15][CH2:16]O)=[O:14].S(=O)(=O)(O)O>C(O)(=O)C>[Cl:11][CH2:12][C:13]([NH:15][CH2:16][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[OH:1])=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 151185-IndanolHCID 62466N-Methylol-alpha-chloroacetamide

Product 1

HCID 212969152-Chloro-N-[(6-hydroxy-2,3-dihydro-1H-inden-5-yl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

134 g (1 mole) of 5-hydroxyindane and 100 g (0.81 mole) of 2-chloro-N-hydroxymethylacetamide are suspended in 300 ml of glacial acetic acid, and 10 ml of concentrated sulfuric acid are added. The mixture is stirred for 30 minutes at room temperature and is poured into ice water. The product is filtered off with suction and recrystallized from methanol.

Workup

  1. filtrationThe product is filtered off with suction
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ecaa98b7278c4f35a2279ce3ff24fee3
Source dataset
uspto-grants-1986_08
Patent number
US04607030

Linked notes

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